Hey gents,

Plenty can happen in a year, especially when you’re taking active steps to improve your personal style.

Today’s Ask the Readers question asks you to be a bit reflective about the journey you’ve been on, and how you’ve been improving, if at all.

From our last “Ask the Readers” segment…

Last Ask the Readers segment got quite a number of guys’ panties in a bunch. This was mostly stirred up by the controversial photo I posted of a man wearing a pair of slim cargos with his suit jacket.

Opinions about this particular combo aside, I was mostly curious about how experimental readers are with their everyday outfits.

Sometimes we fall into a rut. We have the same predictable routine, and we pull out the same clothing day in and day out. On a scale of 1 (strictly rules-based and traditional) to 5 (rules out the window, completely experimental), I asked guys to judge their level of experimentation.

Seemed that most guys are in the middle; a majority answered 3. I’m happy to know that many guys abide by the rules and still venture away from them once in a while. EG is all about internalizing the common style rules and then bending / breaking them as much as you want so you form your own personal style.

Today’s question

So today’s question is a bit different. I want you to reflect on your own personal style journey. You can think back one year, or maybe three or five years if you’re a slow starter.

Is your style better off today than it was a year ago? — click to tweet this

Obviously, personal style is ever-evolving, but just focus on where you are today compared to where you were one, three, or five years ago… whatever time frame you wish to evaluate.

Here are some things to ask yourself:

  • How much better off are you today than you were one year ago?
  • What steps have you taken to improve?
  • What still scares you?
  • Are you happy with the progress you’ve made, and why?
  • What could you still use some help with?

Really looking forward to hearing what you have to say. Leave your comments below!

Some housekeeping at HQ

You may notice the frequency of articles slowing down in the next couple months up until the new year. There’s a lot happening behind the scenes here at EG + 5&B headquarters and it’s getting pretty busy.

1.) I’m starting to release videos

I’ve been looking to do videos for a while now, I just never got around to it. After some well-timed conversations with Antonio and a few other friends with their own sites, I’ve finally gotten my butt in gear.

Long story short, I’m starting to film short tutorials and other style tidbits; they’ll be on YouTube shortly. I hope to regularly add to the channel as much as possible. In the meantime, subscribe to Effortless Gent TV, EG’s YouTube Channel! There aren’t any public videos yet, but they’re coming.

Oh, and I do a semi-regular video series released every (or every other) Sunday, called EG Sundays. Only EG email subscribers get access to these videos.

Don’t want to miss the exclusive stuff? Make sure you get on the list.

2.) Gearing up Fifth&Brannan for fall and winter

If you’re relatively new here, you may not know I also co-founded a clothing label called Fifth&Brannan with my brilliant and supremely talented fashion designer fiancé, Kate.

We specialize in high-end menswear and describe our style as tailored sophistication with a laid-back Californian vibe. These are pieces you want to wear when taking your significant other on a fancy date, if you want to make big moves at the office, or if you just enjoy looking extremely sexy in your everyday life.

We design every piece, our fabric comes from the best mills in Japan and Italy, and we construct everything here in San Francisco.

Anyway, I’m rebuilding our site and looking to launch version 2.0 the first week of December, just in time to feature our new collection.

We’re also planning a pop-up event here in San Francisco, tentatively scheduled for the second weekend in December. In addition to our new collection, we’ll be bringing in some of our favorite complementary brands that carry things like men’s accessories, hats, and grooming supplies, so you’ll be able to find it all in one place, in one weekend!

We’re super excited, but also really busy.

Want to keep up with the latest on Fifth&Brannan? (You should, because our new collection will be killer.) Get on our list to stay updated.

So in case I make myself scarce over the next couple months on the blog, hopefully you understand. We keep the party going on EG’s mailing list though, so make sure you hop on that. We’re also having lots of conversations on Facebook, so feel free to find us on there.

Before you take off, back to our question of the day!

Wait! Don’t just X out of the window. Make sure you give your input to today’s question!

I’m looking forward to hearing your responses in the comments and reviewing them in a future Ask the Readers segment.

Till next time!



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28 Responses

  1. Corey on

    Yes, mine has improved over the past year. I have a job that I am expected to wear a suit and tie every day, so that has made a big difference. Little things like a pocket square, cuff links or a tie clip can go a long way. The biggest thing I have learned is proper fit goes further than anything. If your clothes fit right, you look and feel better-period. This goes for your work and casual clothes. Also, don’t be afraid to try something new. Wearing khaki chinos instead of jeans to an event can really pay dividends. Great feedback from the ladies when you do stuff like this!

  2. David X L on

    Ahh, I’m so stoked! I hope you guys run the event that weekend, because I’ll be in town from Boston.

    I’m way better off now than I was one year ago, largely thanks to this site. My friends are all commenting on the difference, but even then, I now recognize that style is all about caring about oneself, not caring about what other people think. It’s a refreshing perspective shift.

    Right now, I’m trying to buy smart (optimizing for versatility) while I take my clothes to the tailor in small batches. Tailoring really makes the difference, but it can be pricey.

    I’m still somewhat uncomfortable with dressing all the way up with a suit. I work in a business-casual office, and all of my bosses dress casually. In today’s world, it still feels weird to put on a suit for a social occasion unless it’s formal in nature. That’s especially true here in Boston, where mass-produced gray and navy suits define the uniform of every banker douchebag extraordinaire.

    I have a good handle on most things, but I could definitely use more help on the smaller details–things like unusual tie materials, pocket square usage, and man-jewelry. I also need a more detailed understanding of seasonality in dress. I get the basics, but what makes darker cords better for the fall, for instance?

    • Barron on

      Well-said! It’s about caring about oneself, not what others think. In some ways, we dress to impress others (or at least to be presentable in front of others), but when it comes down to it, it’s about the way you feel when you’re looking polished and sharp.

      And hey, you have to dress to complement your surroundings; you don’t always want to stick out (whether it’s in a good or bad way). If your bosses are dressing casually, you can’t always roll up in a suit. Stick to business casual, but really go sharp 100%. Make sure the fit is spot on (like you said), and you’ll be okay.

      Experiment one by one with the questionable items you mentioned. Throw on a cotton or knit tie instead of silk, for instance. It’s all about getting comfortable with things one by one.

      And I think seasonality in regards to dress has more to do with fabric selection than color (has something to do with color, but not always). Things like cords are heavier, thus better to combat the freezing temps. Same goes for heavier wools, thicker cottons, etc. As far as color, darker just seems to “feel” more wintry. Like forest greens, burgundy, charcoal, burnt orange… those just say Fall, don’t they?

  3. John on

    Yes it has improved. I made it a focus this year and began following blogs and picking and choosing who I follow. I’ve also followed several online stores to watch for sales and made a list of stock items to buy. So far my biggest challenge is coordinating items and getting the right fit. I’m thinking I need to find a great local tailor.

    • Barron on

      Finding a tailor can be tough. I suggest testing any potential tailors w/ one item first. Even better if it’s an item you could do without, but would be nice to have. That way, if he Fs up royally, you won’t care so much, and you can move on to the next tailor.

  4. Richard Wilkins on

    I can honestly say that I have made so many strides in the last year that I am even impressing myself. A year ago I knew how I wanted to dress but didn’t really know how to start off in the right direction.

    Today I not only shop less but when I do shop I only buy what fits great and has some quality behind it. Just today I was walking out of my office building and there was a young lady walking my way and she checked out everything I was wearing and it showed on her face that she approved lol. I think the “OK” from a random lady is one of the best compliments a guy can get.

    I think what still scares me is wearing bold colors and slimming down to a minimalist wardrobe, but I’m working on it though. All in all I am very satisfied with the progress I am making and I think this is a positive direction for me both in my personal style and my confidence.

    • Barron on

      I didn’t know it at the time, but a girl I met on the train (now my fiance) said the first thing she noticed when I approached her was what I was wearing. Apparently she approved as well, since she agreed to marry me.

      So yes, I totally agree, getting the A-OK from a random woman is definitely a good reason to step up one’s style game.

      The minimalism will come in time. You’ll notice it naturally happening as you gravitate to a certain set of items every day, then every month, etc. You’ll have pieces that you haven’t touched for say, 6 months or a year. At that point, you will know what can go and what should stay.

  5. Morgan Linton on

    I have definitely improved in the button-down shirt department, think my buying spree this year has really improved my wardrobe. Still think I need to get better jeans, even though I have so many pairs only a few are go-to which means I probably need to get rid of some.

    • Barron on

      At one point I literally had 20 pairs of jeans. All were varying levels of OK when it came to fit. Some I just got tired of (like the wash, or whatever). And I really only had like 2 pair that I wore practically every day. I ended up finally getting rid of the 18 or so pairs I barely touched. So yeah, I feel you there. 🙂

  6. Ryan on

    Yes, I am very happy! I use to dress like a homeschooler with just t-shirts, mamma jeans, and clunky white tennie shoes, pitiful haha now I look like a million bucks… dollars $$ that is not deer 🙂

  7. Chris Myhalsky on

    It’s been less than a year for me, but since starting out on my style journey, I’ve changed quite a bit. My friends are all in rock bands or college althlete wear, and for a long time I tried to dress to fit in, even though it wasn’t my style at all. When I was younger (middle school, I’m only just 21 now) I dressed slightly preppy and got picked on for it, among other things but that’s for another post, which turned me off to being myself. After a cataclysmic life altering event about 8 months ago I reinvented myself and took charge of my style, and I have to say I’ve never been happier, and never looked better. I’ve made huge strides in getting not only the style that I want, but the look that I want as well through learning which brands fit my body shape and who makes the right fit for me.

    • Barron on

      Hey that’s great to hear you started taking charge a few months ago, despite (or maybe because of?) the bad situation.

      When I was 21, I was still figuring everything out. I sorta dressed on trend (bootcuts at the time, admittedly) and was still learning about proper fit. I was also a fat tub of lard, so that didn’t help much.

      But you’re still relatively young, and I’m sure your personal style will keep evolving. As long as you know what your true style is (and it sounds like you do) you can take steps to really grow that, so you’re more confident and assured in what you wear.

      Keep it up!

  8. crockeronline on

    I’m extremely happy with the way I’ve “graduated my style.” It feels great, probably because it coincided with a huge lifestyle shift as well, and I’m fitting into the nicer clothes I’m purchasing. I’m definitely more comfortable on a day to day basis, some days it takes me longer to construct an outfit for the day, and some days it is second nature.
    I presently struggle with lightweight layering (it’s tough to layer in Los Angeles), as well as finding outfits in the world between, casual, comfortable, and professional. But I’ve got plenty of time to experiment and try things out. Each season I’m dressing better than the year before.

    • Barron on

      Love it! Also love that you said you’ve not only graduated your style and fitting into nicer clothes, but you’re more comfortable. That’s awesome.

      Layering can be tough especially in LA (and other places where it tends to be warmer). If it were me, I’d stick with, say, a cotton sport shirt + light cotton or cotton/linen blend sweater. It’s mostly for the transition to evening time when it could possibly get chilly. Or you could do a light jacket (like a Harrington, a cotton field jacket, or something similar).

      If it’s too damn hot, just put on a polo shirt. No biggie.

  9. Dan on

    It’s been less then a year for me. Still in college and my job doesn’t pay much so I can’t build as quick as I’d like but it’s definitely better than last year and I’ve even had many people complement my style and that I’ve changed how I dressed. Reading dappered and effortlessgent has really helped me understand things I wasn’t sure about. I still just have some trouble finding good clothes that fit well and priced well.

    • Barron on

      No rush. If you’re still in college, you have plenty of time. Glad to hear the site’s been helpful, and isn’t it great getting noticed by others? It’s not always the most important thing but it’s definitely a good thing to hear… makes you feel like you’re doing something right. Keep it up!

  10. Dan J. on

    I spent twenty years in the US Navy. I wore uniforms at work and jeans, engineer boots and Harley t-shirts in my off time. I retired in 2005 and got a job as a network engineer doing field work. Working in dusty telecommunications closets all the time, I wore bottom-end business casual – khaki or black cargos and Polos from Walmart or Target. Two years ago, I got promoted to Lead Engineer. I spend most of my time at a desk now – no more dirty closets – and I interface with customers and business partners. I needed to up my wardrobe and I realized I didn’t have the foggiest clue how to dress myself. Suits would be overkill – dress is still business casual. I decided I wanted to go with a casual blazer, long sleeved shirt and slacks. I started with a couple of corduroy blazers from the Mall and started searching the web for a clue on clothing. I now own a dozen blazers (some of them not so casual,) a similar number of dress shirts in various patterns and hues, and I follow this and other sites regularly.

    This morning, I was watching ESPN. The anchor is talking about the Redskins rookie quarterback and I’m thinking “Come on, you can do better than that!” He’s wearing a pinstriped Navy blue suit, a narrow-striped light blue shirt and a tie with similar width stripes. Two patterns I can deal with, but three is pushing the limit, particularly when they’re all the same pattern in similar scale. Plus, he has a spread collar and what looks like a half-Windsor tie knot – much too small to fill the gap. When I’m thinking more about critiquing the anchor’s wardrobe than the football game he’s talking about, then I know I’ve come a long way!

  11. Matto on


    I think in some ways I’ve gone forward, but in other ways I’ve gone slightly backwards. My daily work wardrobe is still black/grey pants, polos, and decent black shoes. Not shabby, but not stylish or memorable either.

    Pro: Now that I read EG/Dappered/TSB daily, I find I’m a lot more knowledgeable around the theory of upgrading my personal style. I can see the benefits of tailored fit, especially given my tall-and-lanky build. Given said build, dressing nicely makes me feel less self-conscious in a business sense, vs just being a tall goof. I’m also understanding more about the build and materials used in quality menswear.

    Cons: I’m not actually putting any of it into practice. I’m still wearing the same year-old pants and polos to work. I’ve got all manner of excuses – the wife makes fun of me when I don’t just grab a t-shirt; it’s a relaxed atmosphere at work; living in a tropical climate it’s hard to wear nice clothes and not look forced (FNQ-AU : there’s no winter here); can’t be bothered ironing my good shirts; got some shirts tailored, then put on 5kg and they don’t fit; can’t afford a second pair of brown shoes due to the custom fit I need; there’s no local shops that cater to men’s style (other than cheap poly Going Out Shirts); baby takes all the spare cash we have; can’t get to the barber this week – it’ll last another week…; etc.

    Long story short, please keep up the good work – I’ll get there eventually.

  12. Felipe Alvares on

    I can say that i wasn’t in a very bad shape, i work in a casual environment (polos, t-shirts and jeans are the norm) but eventually would up my look a little (i use to kid with the guys i say it’s my ‘fashion’ day).

    What improved is now i know that things should fit, stop wearing logos and get better shoes (this one was a painfull lesson).

    I managed to do all that, but my main obstacles are finding the stuff i see on the web (not easy) at an affordable price (so not easy), and adjust the rest of the clothes i already have/have bought (fitted 4 shirts, bought 1 tailored, 1 pant).

    But i’m glad i have more awareness of my outfits. You certainly helped achieve this.

  13. law Abiding citizen on

    I admit that regarding style and dressing up I had no idea of what were the do’s and dont’s, moreover I would end up realizing I was doing something wrong years later.
    Needless to say, this is my go to site for anything stylish and it has been helping me put together some decent outfits for my job interviews and, to some extent, upgraded my casual wardrobe to include some dressy shirts with the right colors for my skin tone instead of the generic t shirt with a random stamp on it.
    inally, I have to thank you for working so hard to help all of those who are clueless as to what makes you stand out of the crowd and what makes you look like a clown.